


Sharp and Delicate

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF
Genre: Breathplay, Choking, Conan O’Brien - Freeform, Cunnilingus, Established Relationship, Explicit Language, Explicit Sexual Content, F/M, Face Slapping, Lingerie, Makeup, One Shot, Rough Sex, Smut, Spanking
Language: English
Status: Completed
Published: 2020-08-08
Updated: 2020-08-08
Packaged: 2021-03-05 19:53:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,087
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25790896
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Conan’s girlfriend convinces him to let her do his makeup...and wear some lingerie. In exchange, Gwendolyn says she’ll do anything he wants, so Conan gets a little rough.
Relationships: Conan O’Brien/Original Female Character
Kudos: 5





	Sharp and Delicate

Sitting at the kitchen table in front of her illuminated mirror, Gwendolyn tapped the brush lightly to remove excess powder before dusting it over her cheek. Suddenly, Conan’s smiling face was reflected beside her, his sharp jaw resting on her shoulder.

“Hey hun, what’re you up to?” He asked, pressing a kiss to Gwendolyn’s neck so as not to ruin her handiwork. 

Reaching back she scrunched her fingers in his buoyant orange hair for a moment before he sat across from her with a glass of water. “Oh, just trying out a new technique I found online.” She selected an eyeliner pen from her pile of makeup and leaned in to the mirror, mouth open. Conan chuckled a little at what he called her ‘Determined Makeup Face.’ “How was your day?”

“Oh, not too bad.” Conan shrugged, crossing one lanky leg over his knee. “Things went pretty smoothly.”

Nodding, Gwendolyn finished applying an eyeshadow. “There!” She turned to face him. “Done.”

Conan grinned broadly, cheeks crinkling a little in the corners. “Beautiful.” He leaned in for a quick kiss. Flipping off the lights on her mirror, something occurred to Gwendolyn. She looked at Conan out of the corner of her eye.

Noticing mid-sip, Conan set his glass down. “What?” He smirked.

Gwendolyn bit her lip, eyes sliding from Conan to her substantial collection of makeup. “You know, you have  _ excellent _ bone structure…”

Catching on, Conan waved his hands in front of him “Oh no,  _ no _ , not happening.” He chuckled and shook his head. 

“Aw, come on…” Gwendolyn got up and, lifting her skirt a little, straddled him in his chair, hands gliding up his chest and nesting in his hair as she brought her face close. “You would look  _ So. Damn. Sexy. _ ” Joining their lips, she swiveled her hips against him and Conan could feel the warmth between her legs even through his jeans.  _ Damn, she can be convincing… _

Gwendolyn broke away and Conan sighed. “Well, alright I guess.” After all, he had to wear a hefty amount of makeup for the show so his translucent skin didn’t make him look like a vampire on camera, and he’d worn beauty makeup for a couple of comedy bits anyway, so it wasn’t a big deal.

Clapping her fingertips together and bouncing up and down on his lap, Conan grabbed Gwendolyn’s ass and pulled her near, but she placed a hand on his chest.

“Later.” She climbed off of him. “Okay, come here.” Directing Conan to pull his chair closer, Gwendolyn began applying. The sheer mass of products was astounding.  _ How could one person need so many things when she’s already so beautiful? _ Unable to see himself, Conan watched as she selected tubes, powders, and liners, occasionally instructing him to look up, close his eyes, or blot his lips. He had to admit it felt nice, the sensation of the tools and brushes delicately painting his cheekbones and kissing his eyelids. 

After dusting his whole face with some kind of loose powder, Gwendolyn leaned back, mouth twisted to the side, staring appraisingly. “Okay. Done.” She nodded, and clicking the light on her mirror, she turned it to face him.

Peering at himself, Conan gasped. “Holy  _ shit _ , I’m...hot.” They laughed as he turned his face this way and that, examining the results. Bright red lips, outlined just a tad past their normal boundaries. Eyelids bedecked with a gradient of green eyeshadows, and surrounded with a dark purple liner. But what really got to him was the way she managed to transform his actual face. His cheekbones looked... _ carved _ somehow, accented with a pleasant peach color, and his already prominent jawline was highlighted in a way he’d never seen before. 

Gwendolyn got up and combed her fingers through his fluffy orange hair. “You sure are.” Standing, Conan put his hands at her waist and leaned in, joining their mutually red lips. She’d used color safe lipstick so it didn’t smear as their mouths explored one another, Conan’s hand creeping down to knead her ass and draw her near as they drank deeply.

Separating from him, Gwendolyn tugged on the front of his shirt. “Hey, would you be willing to take things a little...further, maybe?” She raised an eyebrow and bit her lip.

“What do you mean?” Conan narrowed his eyes.

Crooking her finger in a come-hither gesture, Gwendolyn directed him and he followed her to their bedroom, where she then led him to the closet. Rifling around in a drawer for a moment with her back to him, Gwendolyn turned around to reveal something small, red, and lacy gripped in her hands, eyes trailing gradually up Conan’s long body before reaching his face and smiling mischievously.

“Oh come  _ on! _ ” Conan shook his head, grinning and crossing his arms.

Gwendolyn scooted across the floor to him on her knees. “Oh please,  _ please _ ,” she begged, hands grabbing his thighs and pushing her chin up against his crotch. “It’ll be so hot. And after…” Bringing one of her hands around, she slid it up the inside of his thigh, palming the outline of his cock through the denim. “I’ll let you do anything you want.”

Conan stared down at her, mouth half open, looking up at him lustfully through her eyelashes and kneeling before his cock. He couldn’t say no. “Fine, okay.” He held up his hands in exasperation. Getting up, Gwendolyn smiled and pushed his jacket from his shoulders. Resigned, Conan began unbuttoning his shirt when she reached up to still his hands.

“I wanna do it.” Conan let them fall away and Gwendolyn slowly removed his shirt, tossing it aside before undoing his belt and discarding that as well. Unzipping his jeans, she worked them to the floor along with his boxers, crouching down and instructing him to lift his foot so she could peel off his socks and have him step out of the rest, repeating on the other side. 

When he finally stood before her naked, she picked up the red lace bralette.

“Arms up,” she instructed, and Conan obeyed. Knowing it would be tight on him, as she shimmied it down his torso and walked around him to adjust the back, she came to face him and was glad to see how it flattened the cups across his firm chest. 

Kneeling down, Gwendolyn tapped Conan’s ankle to get him to step into the matching panties, carrying them with her as she rose, and pulling them up in the back over his tiny ass. He was half hard and the miniscule scrap of fabric could barely contain his massive cock. It looked as though he were trying to smuggle a bag of fruit out of a grocery store. Gwendolyn couldn’t resist ghosting her fingers over his length and Conan leaned down with the intention of kissing her neck when she stopped him again.

“One more thing.” Searching in the drawer she pulled out two long strips of sheer fabric Conan couldn’t quite identify. “Point your toes.” Gwendolyn said as she sat on the floor. 

Gathering up the stockings, she carefully snaked them up Conan’s lithe, ivory stems. His legs had always been far nicer than hers. Slender, agile, and toned; they made him look like a supermodel, and she never understood why he was self-conscious about them. 

Once he was fully dressed, Gwendolyn stood up and stared. “Oh,  _ honey _ .” Fingers working through his sparse orange chest hair, they outlined his abs and trailed down to his little belly, coming to rest along his cock as she leaned in to kiss him. “You are  _ so damn gorgeous _ ,” she whispered, catching his mouth and weaving their tongues together as she tugged on his thick cock through the fabric of the panties.

Suddenly Conan broke away, grabbing her upper arms firmly in both hands and looking at her, eyes aflame behind their colorful exterior as he walked her backwards to the bedroom. Reaching the foot of the bed, he spun her around and shoved her face down on the bed.

“Conan!” She gasped. Fisting his hand in her auburn hair, he dragged Gwendolyn’s head back, hot breath against her ear. 

“You said  _ anything _ I want.” Heart beating fast, Gwendolyn nodded and he released her, pulling her skirt and panties to the floor in one fluid motion before kneeling on the floor behind her bent over form. Spreading her with his hands, Conan dug his sharp chin forward and began to lick her from behind, lapping her clit without pretext and sucking lightly. Panting, Gwendolyn bunched her fingers in the sheets and pressed back against Conan’s eager face. Three of his long fingers slid inside and he began fucking her hard with his hand, moaning into her as Gwendolyn started to drip down his contoured cheeks.

“ _ Conan, fuck, FUCK! _ ” She screamed as she rocked into him, and with his free hand he began spanking her, the sting only serving to highlight the immense pleasure between her thighs as her legs trembled and her toes curled into the carpet. Face down on the mattress, Gwendolyn whined a wet spot into the blanket as she came, fluttering around Conan’s fingers as her entire body convulsed.

Standing up, Conan gave her no time to recover, but instead wiped his face on his arm, smearing blush and foundation in the process. He hooked his hands under her armpits and flipped Gwendolyn over roughly only to mount her, spreading her legs with one knee and delicately placing his fingers near her throat, a questioning look in his eye as Conan brought his face near.

Gwendolyn gave him a little nod. “Okay, just remember to pinch me if you need me to back off.” Conan began to apply pressure to the spots just below where her jaw joined her neck. One of his freckled hands was large enough he could easily reach on both sides without applying any undue strain on her windpipe, and as his fingers pulsed, he reached between them to remove his painfully hard cock from the waistband of the panties, smearing it up and down her slick opening before entering.

Rocking into her, Conan stared down at Gwendolyn, crystalline blue eyes sparkling with desire, free hand rubbing a thumb over her clit in time with his strokes. Tipping her pelvis up to meet him, the restriction of air was delicious as the storm rose to a fury inside her, high whines managing to escape as her body constricted around Conan’s sizable cock.

Seeing her eyes roll back in her head, Conan removed his hand immediately and allowed Gwendolyn to catch her breath, settling his hips for a moment until she was able to focus. When her green eyes blinked up at him and gave him a weary smile, he reached up to tenderly caress her face.

Then, without warning, his hand flew across her face with a crack. Twinging and red-cheeked, Gwendolyn faced him again.

“You ready to  _ really _ get fucked?” He asked, narrowing his pretty cerulean gaze at her. Smirking, Gwendolyn nodded. 

Kneeling, Conan snapped up one of the pillows and folded it in half. Lifting Gwendolyn’s ass, he slid it underneath before sheathing himself once more. One hand clamped to her hip, the other twirled over her engorged clitoris as Conan began pounding into her violently. 

Fighting to watch him in between her eyes falling closed in ecstasy and her head ramming against the headboard, Gwendolyn studied Conan. Decorated face awash in bliss, mouth agape as moans dripped from his red lips, colorful lids crinkled tight, sweat gathering in the chest hair above the bralette, lace panties slung low on his hips as he rocketed into her, his nails dug into the flesh of her hip. The sight of Conan tearing into her viciously while dolled up glamorously was too much, and once again a tremor ripped through her, screaming Conan’s name and thrashing wildly.

The contraction around his sensitive cock was overwhelming, and with an unearthly groan Conan came, body curving over Gwendolyn and hips stuttering forward irregularly before collapsing, sweaty and heaving.

Fighting for composure, they held one another, Gwendolyn brushing kisses against Conan’s cheek, unsure if the pink hue was still due to the blush or the result of their passion. Eventually Conan shifted to his side of the bed and Gwendolyn drew her finger over his almost impossibly faint orange eyebrows, dropping down to trace his prominent cheekbone.

“That was fun.” Gwendolyn smiled. “Thank you, beautiful.”

Conan grinned, and once more their bright red lips joined in delight.


End file.
